81290-20-2 | Trimethyl(trifluoromethyl)silane

CAS:81290-20-2 | Trimethyl(trifluoromethyl)silane ,Description

Trimethyl(trifluoromethyl)silane, also known as TMS or TMTSF, is an organosilicon compound with the chemical formula C3H9F3Si. It is a colorless, volatile liquid with a pleasant, sweet odor and a low boiling point. Trimethyl(trifluoromethyl)silane is widely used in organic synthesis, mainly as a source of trifluoromethyl groups. It is also used as a reagent in the synthesis of a variety of organic compounds, including pharmaceuticals, agrochemicals, polymers, and surfactants.
 

Scientific Research Applications

Synthesis of β-Trifluoromethylstyrenes

Trimethyl(trifluoromethyl)silane is utilized in the synthesis of β-trifluoromethylstyrene derivatives through Hiyama cross-coupling reactions. This involves cross-coupling with various aryl iodides, facilitated by catalytic amounts of palladium, yielding moderate to good yields (Omote et al., 2012) .

Radical-Based Reagent in Organic Chemistry

As a radical-based reagent, trimethyl(trifluoromethyl)silane plays a significant role in organic chemistry. It's used for radical reductions, hydrosilylation, and consecutive radical reactions, offering mild reaction conditions with excellent yields and notable chemo-, regio-, and stereoselectivity (Chatgilialoglu & Lalevée, 2012).

Advancements in Synthetic Chemistry

Over the last three decades, trimethyl(trifluoromethyl)silane has evolved as a vital free radical reagent in the synthesis of complex molecules, natural products, polymers, surfaces, and new materials (Chatgilialoglu et al., 2018).

Reactivity with Olefins

Its ability to act as a hydrosilylating agent for olefins and a variety of other organic compounds underpins its versatility in the formation of intermolecular carbon-carbon bonds via radicals (Ballestri et al., 1991).

Use in Silver(I)-Catalyzed Reactions

Trimethyl(trifluoromethyl)silane is involved in silver(I)-catalyzed reactions, such as the efficient generation of 1-(trifluoromethyl)-1,2-dihydroisoquinolines under mild conditions (Wang et al., 2014).

Role in Polymerization

Its strategic role in polymerization, particularly in the photo-induced radical polymerization of olefins and photo-promoted cationic polymerization of epoxides, is noteworthy (Chatgilialoglu et al., 2012).

Application in Perfluoroalkylation

Trimethyl(trifluoromethyl)silane facilitates perfluoroalkylation reactions, aiding in the synthesis of diverse trifluoromethylated purine derivatives (Hocek & Holý, 1999).

Nucleophilic Conjugate Trifluoromethylation

It is used in nucleophilic 1,4-trifluoromethylation reactions with chromones and activated alkenes, highlighting its high regioselectivity and good yields (Sosnovskikh & Roshentaler, 2017).

Copper-Catalyzed Aminotrifluoromethylation

In a copper(I)-catalyzed intramolecular aminotrifluoromethylation process, it serves as the CF3 source, allowing for the creation of various trifluoromethyl azaheterocycles (Lin et al., 2014).

Synthesis of Trifluoromethyl Ketones

Trimethyl(trifluoromethyl)silane is critical in the direct preparation of trifluoromethyl ketones from carboxylic esters, relevant in pharmacology as potential enzyme inhibitors (Wiedemann et al., 1998).

More Information